Check it Off
by strawberriesandsunshine
Summary: Gabriella is a meticulous girl who hasn't done something without planning it in over 10 years. What happens when something spontaneous happens,like she meets an attractively awkward man named Troy Bolton? How does this affect her plan? TXG 2 shot. :D
1. Chapter 1

**A/N: Hello all! It's been a loong time, and I've missed you so much! Really, I have! I've JUST been off for winter break, and I was like, _hey_, _I think I should go back to fanfic because's it's been like, a month, and I miss it like holy freakin hell_. So, here I am! **

**Glimpse into my private life:**

**Woohoo! I feel amazingly good, kicking off my winter break with parties, chilling with friends, and hanging with my yes/no/maybeso "it's complicated" boyfriend, which I like to call, my _boy toy_. (Though he absolutely despises the name). Anyways, I feel utterly deprived though, since the freakout with finals and stuff has limited my dancing time D: So, here's me screaming that I want to be back in the studio! So, my best friend totally rocked her "beginnings" of winter break in ILLINOIS, which made me extremely jealous, because here, in the south, we don't get snow, and she was like, _"It's snowing like FIVE inches, and I played in the snow and had a snowball fight!"_ And I was like. Jealous. I wish it would snow. But it hasn't. At all. *sigh***

**ANYWAYS: **

**This story is kinda...mmm, idk. Kinda spur-of-the-moment-I-have-no-idea-what-I'm-writing. I got the idea from this encounter with my friend last night. She's a major freak when it comes to planning things, and her boyfriend's just like 'chill' with it, and uh, yeah. You'll see. It's based on them, so yeah. Hopefully, I'll let it all out by Christmas. Depends on how my brain's going to work. It's MOST LIKELY going to be a three/four shot. I'm moving up towards writing an actual story! Scandalous :O So, although I've just met them, and briefly chatted to them, I'd like to dedicate this story to the amazing people who PM me because it's been forever since I replied and I feel like I've totally neglected them so, girliesss, this is to you :D**

**ENJOY, and maybe, if you'd like, press that gorgeous green button in the middle that says "REVIEW"

* * *

**

Gabriella Montez was a twenty-year old beast. She was currently enrolled in Harvard Medical School, had a side job as a secretary for the Efron Enterprises, _the_ most elite law firm in the nation, worked her weekends at the soup kitchen and the orphanage, and made cookies on every Friday for her co-workers. In general, Gabriella Montez was the epitome of perfection, nicely gift-wrapped into a box of home-made chocolate chip happiness. When people asked her how she could fit all of this into her life, she was simply shrug and laugh it off, but deep down inside, she knew that it was because of her meticulously planned brain.

Since the age of five, Gabriella Montez had always planned and check-listed her life tightly. Every time spot had to be filled and planned. There wasn't _time_ for spontaneity and surprises. It was a habit that she found useful, and well, it just stuck. She had short-term "checks" and long-term ones. Sure, throughout high school her friends had teased her about it, saying she was uptight and stringent, and sure, sometimes it would limit her social time, but in honesty, it just helped her sort her life out.

However satisfying a completed checklist was, she always found herself worked in a frenzy making said check-list. Like today, when her schedule was packed to each and every second with things to do.

**Finish by today:**

Wake up.** _Check_****.**

Make cookie dough for next batch of cookies. **_Check_.**

Call Mom.**_ Check._**

Eat breakfast. **_Check._**

Call Taylor. **_Check._**

Check on Chad while Taylor is on business trip._ **Check.**_

Finish paper for class on Monday._ **Check**._

Visit kids at orphanage (bring cookies baked last night)_ **Check.**_

Work._ **Check.**_

Suck-up to boss: tell him his new hair cut doesn't make him look like he's missing a patch on the top of his head. **_Check._**

Smile while painfully listening to boss drone on and on about how his wife left him. **_Check._**

Learn to make new potato leek soup for soup kitchen. **_Check._**

Try to convince Sharpay not to drag me to the club tonight.

**Long term:**

Finish med school.

Get promotion at work_. (A/N ok, pretend this is underlined, I kept on trying to underline it but fanfic is being a butt so yeah. sorry for the interruption)  
_

Fall in love.

Get married, give loving, caring mother grandchildren.

Learn to live without a stick up my ass. OH, and buy Sharpay a new car.

Gabriella groaned as she looked at her list, mentally reminding herself to kill her mother and Sharpay for writing on it. Well, at least she finished everything. She looked over her list again.

Shit. Not everything.

_**Try to convince Sharpay not to drag me to the club tonight. **_ Not check.

Before she could go and hide cowardly in a corner, she heard the front door to her apartment swing open and a loud voice scream, " You better be fucking ready because I'm ready to _par_-tay!"

Gabriella groaned as she saw Sharpay walk into her living room, where she was currently sitting with hot tea and fuzzy slippers on.

"Shar-"

"What the fuck are you wearing?"

Gabriella sighed, determined to convince Sharpay not to drag her along.

"I'm not going to the club,"

"Fuck yes you are,"

Gabriella groaned.

"I don't have anything to wear"

"I'll pick something out,"

"I have to call my mom,"

"You just did this morning,"

"I uhm, have to…wash my ears?"

"I'll help,"

Gabriella groaned, knowing that she was not going to win this.

"Shar, I don't wanna go," she tried one last time.

Sharpay looked at her.

"Sucks,"

* * *

Gabriella fidgeted uncomfortably in her seat at the bar, watching Sharpay literally molesting Zeke on the dance-floor. She took another sip of her drink and yawned. Her dress was too skimpy and way too tight. She mentally cursed herself for letting Sharpay force her into the skanky black dress hidden in the back of her closet that barely covered her ass and her breasts. Sharpay said it made her look less like a nerd, and out of place in a club. Puh-lease. It was her_ job_ to look like a nerd.

"Oh, and _try_ to be a little more interesting. Don't tell them you're a med student. Tell them you like, strip for people," she had said while Gabriella merely rolled her eyes.

As she set her glass down and asked for another, she felt a presence next to her.

"Hey, can I get another one of these,"

Gabriella turned and saw the most attractive man her dear eyes ever had the pleasure of looking at. Her eyes trailed from his dirty blonde hair down his face and onto his hardened and chiseled body. Unbeknownst, the man was watching her the entire time, slightly chuckling to himself, but also in awe of the beauty in front of him. Deciding to break her of the trance she seemed to be in, he cleared his throat.

"Uh, can I help you?"

Gabriella's eyes shot up and instantly melted in his. "Uhm, sorry," she squeaked before blushing, knowing he had caught her staring.

The guy chuckled as the bartender set his drink in front of him. He picked it up and turned to her before saying, "Troy Bolton,"

Gabriella nodded. "Diet Coke,"

Troy looked at her oddly as she picked up her own glass and took a sip. He smiled widely and immediately let out a chuckle.

"Uh, no. That's not a drink. That's my name. Troy Bolton,"

"Oh," Gabriella said before immediately blushing again. "Uhm, Gabriella Montez," she said.

Troy grinned. Her name seemed almost perfectly fitting to her. He was immediately intrigued by her: the dark brown curls that framed her innocent face and the way it would turn red whenever he talked to her. "Diet coke?" he asked, motioning to the glass of the bubbling liquid.

Gabriella couldn't help but feel her face heat up again. How embarrassing. What twenty-two year old went to a bar and ordered a diet coke. "Uhm…yeah," she said awkwardly. "I-uh, I'm not a big drinker,"

Troy smiled. "Me neither," he said, holding out his glass. "It's lemonade,"

Gabriella couldn't help but let out a giggle.

He chuckled. "It's good," he replied before taking another sip and facing her. "So, what do you do?"

"I'm a medi- I rob stores" she replied, cursing herself for actually listening to Sharpay. And then, mentally beating herself for saying the first and most stupid thing she could say.

He looked slighty shocked before replying, "Oh. That's uhm-nice,"

Gabriella nodded dumbly while attempting to swallow all the Diet Coke in one gulp to avoid looking at him.

"So, you rob stores?"

"No. But my friend, see the one with her hands down that guy's pants, said to lie so I would seem more interesting,"

Troy nodded. "That makes perfect sense,"

Gabriella nodded before suddenly hearing her cell phone beep. She looked down and realized it was her alarm that she had set, reminding her that it was almost midnight, and she had to get home because she had class tomorrow.

"Oh shit," Gabriella said before looking up at Troy who had a curious expression on his face.

"What's up?" he asked, still holding on to her hand.

Gabriella sighed internally as she felt his thumb grazing the back of her hand. There was this strange attraction between her and this _Troy_. "I uhm-mmm,"

Troy grinned.

"Uh- what's the question?"

Troy didn't say anything before leaning down and gently connecting their lips. After a few minutes he released her lips and smiled at her content look.

"I don't remember, but I'm pretty sure, that's the answer," Troy replied.

Gabriella just grinned stupidly and licked her lips before suddenly frowning. This was _not_ like her at all. She _seriously _ didn't kiss guys randomly, and she _especially_ doesn't do it with a stranger she just met like, five minutes ago. For all she knew he could be a _seriously _serial killer. That was _definitely_ not on her check list. Make out with a murderer before being seriously kidnapped and killed. _Seriously._

Gabriella eyed Troy as he looked at her curiously, trying to figure out why she suddenly seemed a _lot_ less interested in him. He wasn't going to deny it. He'd never felt this strange type of attraction to a woman before, especially one he just met. Oh God. What if she was a lesbian? Not that there'd be anything wrong with it, in fact it would be slightly hot, but that would explain why she was looking at him like that. Oh God.

_He doesn't look like a murderer. _

"Uhm, listen. I hope I didn't freak you out just then. It was kind of, just, something. You know? I felt this kind of electrical spark between us and I thou-"

"Is that _blood_?" Gabriella interrupted, pointing at a blotch on his jacket. Troy looked down and realized the stain from the chocolate syrup he had attempted to put on his ice cream earlier. Shit.

"Uhm, no. It's probably from-"

"You hacking a poor innocent person over with an ax. Oh. MY. God. I knew it," Gabriella said, more than just a hint of panic in her voice.

"Gabriella-"

"Just when I meet some decent guy, he has to be a serial murderer," Gabriella panicked before frantically looking around for her purse. "Sorry, Troy, but uhm, I have to go. Have fun stabbing-I mean staying- in uhm…err.-… where are we?"

Troy had an amused look on his face when he answered, "Boston,"

"Right, Boston. Yup," she continued while grabbing her black clutch. "It was nice meeting you, and-"

"Gabriella," Troy said, gently grabbing onto her arm. "I'm _not_ a serial killer,"

Gabriella nodded disbelievingly while nervously looking at the hand grabbing onto her arm. "Uhhh huhh,"

"I'm not going to kill you,"

"uhh huh, yeah, my arm-,"

"The stain's just chocolate,"

"uhh huh…oh,"

Gabriella sheepishly smiled as she managed to somewhat sit back down on the stool, her face red. She awkwardly looked up. "Sorry for confusing you with a deadly ax-murderer"

Troy smiled. "Happens all the time,"

Gabriella grinned back before her cell phone beeped again. "Oh, crappers,"

Troy continued to look at the girl sitting in front of him curiously. She _really_ wasn't like anyone he had ever met. Ever. He couldn't help but be more than just a little intrigued by her. As he watched her frantically shove her phone back into her bag and get up, he rose with her.

"What's up?" he asked, for the second time that night.

"I have to get home. I have a class tomorrow," she replied.

"Robbing banks 101?" Troy asked, smirking.

Gabriella giggled. "Yeah. It was nice meeting you, Troy,"

Troy smiled and watched her leave the bar. God, that woman was amazing. He felt so interested in her, and he knew that no matter what, he _had_ to be with her. He wasn't sure what compelled him to do so, but seconds later, he found himself running out of the bar and standing next to a surprised Gabriella.

"I'll walk you," he said, slightly out of breath.

Currently, the only thing running through Gabriella Montez's mind was _Serial Killer Serial Killer Serial Killer_.

But she pushed it aside when she found the tingly feelings rushing through her hand when he grabbed it.

"Sure," she said, and they began the long trek home.

* * *

Part Uno: Done :D

Hooray :D now, tell me what you think by pressing that gorgeous green button. Right there.

Hopefully, I can have part two up tomorrow? Reviews fuel fingers.

...ok not literally, but figuratively. And, yeah. Mk, that didn't make much sense, but still.

I LOVE YOU ALL :D

C: strawberriesandsunshine


	2. Chapter 2

**A/N: **Hi everyone! First of all, HAPPY CHRISTMAS EVE! WOOHOO! I'm _so_ extremely excited for tomorrow, and tonight, because I'm going to spend it with my best friend in the _whole_ entire world, and we're going to make cookies and sing and dance and yeah. I love Christmas Eve. Love. it. And for people who don't celebrate Christmas,

HAPPY CHRISMAHUANNAKWANZIKAH! (sorry if I totally misspelled that)

So, I hope you guys have _the _most awesomest holiday ever. This is not the last chapter because I have something else planned for the next chapter. Which I haven't written yet, but hopefully I'll think of something. I'm sorry for keeping you guys waiting (not updating yesterday) but my brain wasn't functioning. This chapter. Eh, I'm not quite sure if I like it too much, but I _mean_ I don't know. Let me know what you think.

I think I _might_ scribble out a Christmas one-shot for tomorrow, or update tomorrow. One of those. :D

So, yeah! Happy Holidays if I don't get the chance to say it tomorrow, and well, REVIEW :D

Oh! I almost forgot! Thanks to these _amazing_ reviewers who make me smile everytime I read them:

Gabbylynn93, 12superstar, .girl.t.g, stardust, , superstar22, xdude.i', 1HSMWiLdCat, glaceauxfraises, karebarekeke, and HSMandChelseaFCfan.

And karebarekeke, I want that cookie. :D

SO ENJOY :D

* * *

Gabriella was a planner. Gabriella was not spontaneous. However, bringing a stranger into her home at midnight from a club was pretty spontaneous…and slightly dangerous.

"Nice home," Troy commented while peeling off the scarf and his thick outer coat. The apartment wasn't really that big, but it had a homely feel to it, and smelled like vanilla peppermint. It just screamed her.

"Thanks," Gabriella muttered. She was freaking out on the inside. What the _hell_ had she been thinking? They had reached her apartment, and he had sweetly pecked her on the lips. Awkwardly, yes, but sweet. Then, out of the blue, she asked him if she wanted to come in, knowing _perfectly_ well that she had an early class tomorrow, and knowing _perfectly_ well, what "inviting in" was insinuating. Plus, she didn't do "out of the blue". Gabriella Montez, ever since the age of five, has not done "out of the blue".

What. The. Hell.

"Tea?" she asked while making her way into the kitchen. Troy nodded and settled himself down on the couch.

Who drank tea? He didn't. Not at all. He thought it was possibly the most disgusting drink on the earth. However, he would drink _anything_ if it meant being with Gabriella. He glanced around. On the walls were pictures of her and other people, probably family and friends.

Suddenly, he heard a crash come from the kitchen, and bolted up. "Need help?" he called out.

"Please?"

Troy walked into the kitchen to see Gabriella on the floor, surrounded by various pots and pans. Troy smiled at her defeated look when pointing to the tea pot resting on the highest shelf.

"I don't normally keep it up there, but my friend came over and put it there in an effort for me to leave the house," she mumbled.

Troy nodded and helped her up before reaching with ease, and grabbing the teapot. Smiling as he imagined be her 'knight in shining armor,'

"Thanks,"

As she made the tea and they proceeded back into the living room, Gabriella yawned.

"Tired?" Troy asked, pretending to sip from the cup.

"Mmm. Sorry. I don't usually stay up this late," she said before realizing how much of a teenager she sounded. Troy chuckled at how cute she was.

"If you want me to lea-"

"No, it's fine!" Gabriella said quickly, strangely liking the feeling this stranger had on her. She yawned again. "I just. Mmm. I'm really tired,"

Troy wrapped an arm around her and brought her head to his shoulder. "Sleep," he said as she rested her head onto his chest and snuggled into him.

"Mmmk,"

* * *

Gabriella woke up to the bright and glorious lights shining upon her. She spotted the clock and nearly had a heart attack. It was 9:30! Why didn't her alarm clock ring? She looked around and realized she wasn't on her bed, and the events of last night raced back into her mind.

Shit.

Shitshitshitshitshit.

She pushed Troy's arm wildly and began freaking out.

Troy woke up when he felt his arm being nearly flung out of his socket. The first thing he saw was the angel he met last night, jumping up and down anxiously. He yawned.

"Have to pee?" he asked and sat up. Gabriella whirled her head around and screamed suddenly.

"You're…awake" she stated. Troy nodded and stretched.

"Good morning sunsh-"

"Oh. My. God. I'm in so much shit. I'm late for class. I have to go," she said before bolting into her shower and almost jumping in with her clothes on. After probably the fastest shower of her life, she ran out of her bedroom and grabbed to see her checklist for today. After reviewing that she has lost at least three precious hours from waking up late, she let out a frustrated yell. She had already missed the two classes she was supposed to take today. Next, she was supposed to be baking toast for the sandwiches at the Soup Kitchen. She ran out the bedroom in sweats to see Troy calmly sitting on her breakfast bar, peeling a banana.

"Why are you peeling a banana!?" she asked.

Troy shot his head up. "Oh, sorry, I was kind of hungry and-"

"AH!"

Gabriella has never felt this way before. Her plan. It was completely ruined. For the first time in seventeen years, something accidental had happened. Something she had not planned. Then, it had messed up her checklist. It felt like her perfectly balanced life was now rushing down the drain. She would never be able to finish medical school now, and she would never be able to balance school, volunteering, and everything else. It felt like her world had collapsed, the perfect framework of her life. She had this gut-wrenching feeling inside her stomach, knowing that she couldn't keep everything completely in line.

Troy saw Gabriella anxiously begin to jump around again, and he offered her the banana.

"Banana?"

Gabriella almost ripped the banana from his hands and shoved it into her mouth before collapsing onto the floor, almost in tears.

Troy immediately got off of the chair and sat down by her. "Hey, you ok?" he said, soothingly rubbing his hands up and down her back.

Gabriella sniffled and was very close to wailing, but understood that, although she felt she had connected with this man, he was still a stranger when it came to sobbing hysterically on his shoulder. She couldn't speak and when she opened her mouth, she choked on a sob.

Troy seemed to understand and pulled her closer to him. "Shhh, it'll be ok," he said, realizing that she probably wouldn't want to talk to him now. "Come on, I know something that'll make it all better,"

* * *

An hour later, Gabriella and Troy were sitting under what Troy called his "Freedom Fort," which consisted of a bunch of blankets hurled around Gabriella's living room, covering things. They were leaning against the couch while sitting on the floor while Gabriella was sipping tea and Troy (after searching tirelessly) found coffee and was drinking it.

Gabriella sighed, and looked at the man sitting beside her. He was so perfect in every way. Sure, she had just met him, but she never felt this connection before. He had taken away her fears and just soothed her under the thing he called his fort. Gabriella giggled at how child-like he was.

Troy turned his head at the sound of her giggle. "Feeling better?" he asked, shifting a little so the arm wrapped around her was tracing circles on her shoulder.

Gabriella nodded and leaned into him.

"Wanna tell me what's wrong?"

Gabriella sighed again, and she set her tea mug on the floor, hoping that it wouldn't spill. She turned herself so she could look at him directly.

She pulled a folded piece of paper out of her sweat pants and put it in Troy's hand. "My life revolves around that," she said.

Troy, hoping it wasn't a picture of another guy, opened it and saw it was just a simple list of things.

"It's a checklist," he remarked. Gabriella nodded.

"I-I'm meticulous. I'm annoying. I plan everything to the last detail. Everything on the checklist must be checked off," she said, beginning to feel frustrated again. She rested herself back against the couch to try and calm herself down.

Meanwhile, Troy wasn't sure what was going on. It was just a checklist. He was sure millions of people had it.

After a while of silence, Gabriella looked at him again.

"I can't be with you," she said.

Troy felt his heart break right there. "Wh-what?" he asked quietly. "Why not?"

Gabriella sighed. "I-it's not on the checklist," she said.

Troy groaned. "What's up with you and the checklist?" he asked.

Gabriella thrust her hands into her hair. "It's _everything_, Troy. You know what happened with you here today, Troy? I didn't check off the first two! I'll never be able to check those off! It'll be the first time in over ten years that I haven't been able to check everything off of my checklist!"

"…and it's because of me?"

"YES!" Gabriella said. "Last night, I was supposed to sleep at eleven-thirty because I had an early class this morning, but something about you clouded my judgement. I ended up talking to you for another hour! Then, I ended up inviting you in, and then we fell asleep on the couch, and I missed my classes!"

"They're just classes!" Troy said, feeling some kind of anger from being denied rise up.

Gabriella groaned. "It's not _about_ the classes! It's about the checklist and how my life is no longer stable!"

Troy looked at the checklist in his hands. It seemed to burn him. "It's about this? Gabriella, you can't _plan_ everything in your life! Things _will_ happen! Things unexpected and things totally random _will_ happen! You can't plan all of them!"

Gabriella sat quietly and looked at Troy, tears beginning to swim in her eyes again. So many people had told her that before, but somehow, Troy saying it made her feel different. She really felt something with Troy, but she knew it would get in the way of her life.

"For once, Gabriella, realize you can't plan everything!"

Gabriella contemplated it. If she hadn't gone to the club like she had tried not to, she wouldn't have met Troy. If she hadn't have talked to Troy at the bar, she wouldn't have felt the butterflies swishing around all over her body. If she hadn't invited Troy in, she wouldn't have fallen more and more in whatever she was feeling now with him. She looked up at him.

"Troy. I really like you,"

Troy's heart soared.

"But, it's my checklist, my balance, Troy," she said.

He felt his heart plummet down. "Fuck your checklist, Gabs," he said, trying to get through to her again.

"I-I can't" she said.

Troy crumpled up the checklist he was holding and heard Gabriella gasp in shock. "Fine," he said. "But look at your checklist, and I'll think you'll find that, as much as you didn't want to, I fit in at number sixteen,"

With that, he threw the checklist down and moved out from under their fort. "See you later, Gabriella," he said.

She began to cry again and heard the door slam closed on its way out. Dejectedly, she crawled and retrieved the crumpled piece of paper and opened it, gasping at number sixteen.

_**Fall in love. **_

Did she love him? Granted, she felt a strange attraction to him. She felt that they were something special. She really liked him, like really really really liked him. Was she ready to throw it all away, just because of a checklist?

She scrambled out from under the canopy she and Troy had made before running out the door, looking madly for the dirty blonde who had captured her heart.

"Troy!" she shouted and began running down the stairs and finally onto the main street. She didn't spot him anywhere. The loudness of the busy street mixed with the rush of people around her and she frantically darted her head left and right, hoping to catch some glimpse of him. Feeling utterly devastated, she turned to go back inside before hearing her name.

"Gabriella?"

She turned around and saw Troy, standing there, coming out of the coffee shop right next to her apartment building, holding a mug of coffee.

"What-"

"No offense but the coffee sucked at your place," Troy said, smiling as he saw Gabriella holding up the rustled piece of paper in her hands.

"Do-do you mean it?" she asked, all of a sudden, focusing on number sixteen.

"I don't love you, Gabriella. Not yet, at least," Troy said while walking towards her. "But I know I will,"

Gabriella looked at him and saw him look at her. "You can't say that you don't at least want to try,"

"I do," Gabriella muttered before grinning at him. She smiled and ran up to him while he wrapped his arms around her waist, dropping the coffee. She breathed in his scent and realized that she wouldn't have minded just staying in his arms forever. She pulled her head out from his neck and met his lips with hers.

"So no more freaking out?" Troy asked when they had pulled apart.

Gabriella agreed.

"And no more of this 'I can't be with you' business,"

Gabriella nodded.

"And one day, Gabriella. I promise, I'll love you. You can check that off your checklist,"

* * *

OK, this chapter was 2160 words, but it _definitely_ looks really short. Hmm, idk. Anyhoo. I hope you enjoyed it and I hope my brain will function enough after all the delicious food and Holiday craze tonight that I will be able to write something _totally_ awesome for tomorrow.

Again, HAPPY HOLIDAYS!

C: strawberriesandsunshine


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